EP1591510B1 - Organische elektrolumineszente Vorrichtung mit einer Emitterschicht, die das Tetracarbazolbiphenyl enthält - Google Patents

Organische elektrolumineszente Vorrichtung mit einer Emitterschicht, die das Tetracarbazolbiphenyl enthält Download PDF

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Publication number
EP1591510B1
EP1591510B1 EP05007241A EP05007241A EP1591510B1 EP 1591510 B1 EP1591510 B1 EP 1591510B1 EP 05007241 A EP05007241 A EP 05007241A EP 05007241 A EP05007241 A EP 05007241A EP 1591510 B1 EP1591510 B1 EP 1591510B1
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EP
European Patent Office
Prior art keywords
electroluminescence device
organic electroluminescence
organic
emitting layer
anode
Prior art date
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Application number
EP05007241A
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English (en)
French (fr)
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EP1591510A2 (de
EP1591510B8 (de
EP1591510A3 (de
Inventor
Jeong Dae Seo
Hyun Cheol Jeong
Chun Gun Park
Kyung Hoon Lee
Jae Man Lee
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LG Display Co Ltd
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LG Electronics Inc
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C5/00—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work
    • B05C5/02—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work the liquid or other fluent material being discharged through an outlet orifice by pressure, e.g. from an outlet device in contact or almost in contact, with the work
    • B05C5/027—Coating heads with several outlets, e.g. aligned transversally to the moving direction of a web to be coated
    • B05C5/0275—Coating heads with several outlets, e.g. aligned transversally to the moving direction of a web to be coated flow controlled, e.g. by a valve
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C5/00—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work
    • B05C5/002—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work the work consisting of separate articles
    • B05C5/004—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work the work consisting of separate articles the work consisting of separate rectangular flat articles, e.g. flat sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05C5/00—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work
    • B05C5/02—Apparatus in which liquid or other fluent material is projected, poured or allowed to flow on to the surface of the work the liquid or other fluent material being discharged through an outlet orifice by pressure, e.g. from an outlet device in contact or almost in contact, with the work
    • B05C5/0254—Coating heads with slot-shaped outlet
    • B05C5/0258—Coating heads with slot-shaped outlet flow controlled, e.g. by a valve
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to an organic electroluminescence device, and more particularly, to a blue phosphorescence organic electroluminescence device.
  • An organic electroluminescence device according to the preamble of claim 1 is known from WO 2004/074399 A1 .
  • OLED organic light emitting diode
  • the organic electroluminescence device is a device emitting light in a following manner. First of all, if electric charges are injected in an organic layer between a cathode and an anode, a pair of electron and hole is formed to disappear. While disappearing, the electron/hole pair emits light.
  • the organic electroluminescence device which can be formed on a flexible transparent substrate like plastics, is drivable at a voltage (below 10V) lower than that of a plasma display panel (PDP) or an inorganic electroluminescence (EL) display.
  • a voltage below 10V
  • PDP plasma display panel
  • EL inorganic electroluminescence
  • the organic electroluminescence device needs relatively low power consumption and provides the excellent color sense.
  • ETL electron transport layer
  • EML emitting layer
  • HTL hole transport layer
  • an anode material is coated on a transparent substrate.
  • ITO indium tin oxide
  • a hole injection layer (HIL) is coated on the anode material.
  • Copper phthalocyanine (CuPC) as the hole injection layer is mainly coated 10 ⁇ 30rum thick thereon.
  • HTL hole transport layer
  • An organic emitting layer is formed thereon. In doing so, a dopant is added thereto if necessary.
  • a dopant is added thereto if necessary.
  • 4,4,'-N,N-dicarbazolebiphenyl(CBP) as the organic emitting layer is deposited 30 ⁇ 60nm thick.
  • bis(2-(4,6-difluorophenyl)pyridyl-N,C2')iridium(III) picolinate (named Firpic) is mainly used as the dopant.
  • An electron transport layer (ETL) and an electron injection layer (EIL) are sequentially coated thereon or an electron injection transport layer is formed.
  • a cathode is coated thereon. And, a protecting layer is finally formed thereon.
  • the present invention is directed to an organic electroluminescence device that substantially obviates one or more problems due to limitations and disadvantages of the related art.
  • An object of the present invention is to provide an organic electroluminescence device, by which high brightness is provided in a manner of using a host substance of an emitting layer.
  • an organic electroluminescence device includes an anode, an organic emitting layer on the anode, and a cathode on the organic emitting layer, wherein the organic emitting layer has a configuration of Formula 1 and Formula 2,
  • An organic electroluminescence device can be formed by sequentially stacking an anode, a hole injection layer, a hole transport layer, an organic emitting layer, an electron transport layer, an electron injection layer and a cathode.
  • the organic emitting layer can be formed of a host material having the configuration of Formula 1.
  • the host material of Formula 1 is 3,3' ,5,5' - tetracarbazolbiphenyl (TCBP) that is synthesized in a following manner.
  • TCBP 3,3' ,5,5' - tetracarbazolbiphenyl
  • tributylmagnesiumchloride (8.73mL, 0.017mol) and anhydrous THF (50mL) are put in a dry round-bottom 2-neck flask and are then agitated. Subsequently, 2.5M n-BuLi (14.0mL, 0.035mol) is slowly dropped thereon and agitation is performed for 10 minutes at 10°C.
  • 1,3,5-tribromobenzene (10g, 0.031mol) and anhydrous THF (50mL) are put in the flask to be agitated.
  • titanium chloride (3.4g, 0.021mol) is injected using a syringe to be agitated for 2 hours at 0°C.
  • the reactant solution is poured in an ammonium chloride solution (100mL) to be agitated for 30 minutes. Extraction is performed thereon with ethylacetate and washing is performed using distilled water (300mL).
  • toluene is removed by a rotating evaporator.
  • Mixture is put in distilled water (200mL) to be agitated for 30 minutes.
  • Precipitant is filtrated to be washed using hexane (200mL).
  • ITO indium tin oxide
  • glass is patterned to have an emitting size of 3mm x 3mm. And, a cleaning process is carried out on the patterned substrate.
  • NPD Firpic
  • BAlq 3 BAlq 3
  • Alq 3 Alq 3
  • the organic electroluminescence device includes the organic emitting layer having the host and dopant materials between the cathode and the anode and forms the organic emitting layer using the host material in Formula 1, thereby obtaining the blue phosphorescence organic electroluminescence device of high brightness.

Claims (4)

  1. Organische elektrolumineszente Vorrichtung, umfassend:
    eine Anode;
    eine organische emittierende Schicht auf der Anode; und
    eine Kathode auf der organischen emittierenden Schicht,
    dadurch gekennzeichnet, dass die organische emittierende Schicht eine Konfiguration aus Formel 1 und Formel 2 besitzt:
    Figure imgb0013
    Figure imgb0014
  2. Organische elektrolumineszente Vorrichtung nach Anspruch 1, wobei die organische emittierende Schicht weiterhin Formel 3 umfasst:
    Figure imgb0015
  3. Organische elektrolumineszente Vorrichtung nach Anspruch 1, wobei die organische emittierende Schicht weiterhin Formel 4 umfasst:
    Figure imgb0016
  4. Organische elektrolumineszente Vorrichtung nach Anspruch 1, wobei die organische emittierende Schicht weiterhin Formel 5 umfasst:
    Figure imgb0017
EP05007241A 2004-04-09 2005-04-02 Organische elektrolumineszente Vorrichtung mit einer Emitterschicht, die das Tetracarbazolbiphenyl enthält Active EP1591510B8 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR2004024524 2004-04-09
KR1020040024524A KR100556421B1 (ko) 2004-04-09 2004-04-09 청색 인광용 유기 전계 발광 소자

Publications (4)

Publication Number Publication Date
EP1591510A2 EP1591510A2 (de) 2005-11-02
EP1591510A3 EP1591510A3 (de) 2005-11-09
EP1591510B1 true EP1591510B1 (de) 2008-05-21
EP1591510B8 EP1591510B8 (de) 2009-01-07

Family

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EP05007241A Active EP1591510B8 (de) 2004-04-09 2005-04-02 Organische elektrolumineszente Vorrichtung mit einer Emitterschicht, die das Tetracarbazolbiphenyl enthält

Country Status (6)

Country Link
US (1) US20050227113A1 (de)
EP (1) EP1591510B8 (de)
JP (1) JP5179706B2 (de)
KR (1) KR100556421B1 (de)
CN (1) CN100428528C (de)
DE (1) DE602005006882D1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100556422B1 (ko) * 2004-04-19 2006-03-03 엘지전자 주식회사 청색 인광용 유기 전계 발광 소자
JP2008147354A (ja) * 2006-12-08 2008-06-26 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子
DE102008036982A1 (de) * 2008-08-08 2010-02-11 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
JP4500364B1 (ja) * 2009-08-31 2010-07-14 富士フイルム株式会社 有機電界発光素子

Citations (1)

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Publication number Priority date Publication date Assignee Title
WO2004016711A1 (en) * 2002-08-16 2004-02-26 The University Of Southern California Organic light emitting materials and devices

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JPH05263073A (ja) * 1992-03-17 1993-10-12 Sumitomo Chem Co Ltd 有機エレクトロルミネッセンス素子
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Also Published As

Publication number Publication date
KR100556421B1 (ko) 2006-03-03
EP1591510A2 (de) 2005-11-02
CN1681364A (zh) 2005-10-12
DE602005006882D1 (de) 2008-07-03
KR20050099270A (ko) 2005-10-13
JP5179706B2 (ja) 2013-04-10
US20050227113A1 (en) 2005-10-13
EP1591510B8 (de) 2009-01-07
EP1591510A3 (de) 2005-11-09
CN100428528C (zh) 2008-10-22
JP2005302722A (ja) 2005-10-27

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